Leadership & Strategy

If I Only Knew Then What I Know Now, Managing Would Be Easier

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Last Updated: March 17, 2025

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Young boy in a suit and glasses looking thoughtful, standing in front of a chalkboard with drawn lightbulbs, symbolizing leadership growth and managerial wisdom. Text reads 'If I only knew then what I know now.' Branding for Resourceful Manager and HR Morning included.

Hindsight is worth its weight in gold and keeps us from repeating our mistakes.

So you might find yourself saying, “If I only knew then what I know now …”

Take a moment and think about it. What do you truly wish you knew now that you didn’t when you stepped into a leadership role?

Managing Yourself

If you could go back in time to that first management position, what single piece of knowledge would you take with you to make managing easier or better today?

To get some real-world answers, we went straight to people on the front lines – executives and supervisors we respect – and here’s what they told us:

1. Share Failure

If a direct report is failing at his job, he isn’t solely to blame. The manager shares in that blame, too.

It’s a manager’s job to train, empower and motivate employees. If a direct report is failing, then as the manager you have to ask yourself if you’ve done everything you can and given the employee everything he needs to do the job successfully. Employees often fail because they aren’t given the proper tools, procedures, or support to succeed.

2. Listen More

One trait successful managers have is they’re good listeners on a variety of levels:

They listen to and focus on their employees’ concerns, wants and needs.
They listen to the “old pros.” Even if they don’t agree with them, they’ve been there and done that, and you can learn from their experiences.
They listen to and understand what the company’s real mission and goals are. They fully understand them so they’re not making decisions in a vacuum.
They listen to their own gut. If it feels wrong, they usually don’t do it — even if others say they should. Investigate deeper until you know what’s causing the issue.

3. Lighten Up

Yes, being a manager is an important job, but you don’t have to be serious 100% of the time.

A lot of first-time managers think they have to establish the fact they’re the boss by being rigid and demanding control of everything. But all that does is make them unapproachable and put distance between them and their employees.

Being approachable and accessible garners trust, and when employees trust you, they work harder for you.

4. Don’t Worry About Being Liked

Most people want to be liked. And being liked is great, but as a boss you can’t worry about it too much. If you’re focused on being liked by your employees, then that’ll monopolize your time and you won’t be focused on the issues that are really important.

Remember: You can please some of the people some of the time, but you can’t please all of the people all of the time.

Be fair, trustworthy and pleasant, and your employees will follow your lead.

5. Be Friendly, but Don’t Be Friends

While being friendly and approachable is a good thing, being “friends” with your direct reports isn’t. It often leads to favoritism and resentment from employees who aren’t in the “friend” category.

It also affects a manager’s authority: A friend may think he doesn’t have to follow certain rules and that he’s above the other employees. This greatly complicates the employee/boss relationship. Give employees opportunities to become friends with each other, but don’t get entangled in the friendships.

6. Don’t Try to Fix Everything at Once

Doing so will only lead to frustration and failure. Take baby steps and remember, it didn’t break all at once either.

Fix one or two things at a time. Once you have a handle on that or your employee has a handle on something, go back and work on the next issue.

The fact that you stay calm and tackle things one at a time, instead of becoming frantic and irate, builds rapport and, eventually, respect.

Editor’s note: When I heard my colleague share this tip, it reminded me of a personal trick. I call it the Black Diamond Rule. When I was learning to ski the most difficult ski slopes, I was terrified looking down the whole hill. Then I learned to tell myself, “You don’t have to ski the whole thing. You just need to get over there.” It was a short, albeit steep, distance from where I stood. When I got there safely, I told myself the same thing again until I conquered the hill. The Black Diamond Rule works under all kinds of stressful situations.

7. Don’t Assume Anything

People are complicated beings and many things can influence how they communicate. That’s why it is so important not to assume anything.

If something isn’t clear, ask questions until it is. If you’re explaining something, have the person you’re talking to explain it to you. Ask if they have questions. Keep the communication channels open.

8. Show People Emotions Count

Like it or not, how someone feels affects everything they do.

Asking employees to leave their emotions at home doesn’t work. It creates a stressful and unpleasant work environment.

And emotions play a major role in how people learn. It’s been shown that people absorb more information if they’re relaxed and having fun. If they’re stressed, scared or upset, concentration and comprehension flies right out the door. So even if someone is slow to pick something up, stressing them out more doesn’t help.

9. Lay a Strong Foundation

Giving a new hire too much too fast leads to having to backtrack later and re-teach the basics that should have been taught in the beginning.

Taking the time to lay a strong foundation of the basic skills and core knowledge of a job with new hires first helps both the manager and new hire in the long run.

10. Don’t Dwell on Mistakes

First-time managers make mistakes. Accept the fact and move on. No one’s perfect.

Embrace your mistakes and learn from them. Dwelling on mistakes will whittle away your confidence and make you start to second guess just about everything you do.

And let’s face it, most management skills are best learned by doing.